EP1088014B1 - Teil-interpenetrierende polymernetzwerke - Google Patents

Teil-interpenetrierende polymernetzwerke Download PDF

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Publication number
EP1088014B1
EP1088014B1 EP99928811A EP99928811A EP1088014B1 EP 1088014 B1 EP1088014 B1 EP 1088014B1 EP 99928811 A EP99928811 A EP 99928811A EP 99928811 A EP99928811 A EP 99928811A EP 1088014 B1 EP1088014 B1 EP 1088014B1
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EP
European Patent Office
Prior art keywords
functional
polyurethane prepolymer
polyurethane
diisocyanate
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP99928811A
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English (en)
French (fr)
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EP1088014A1 (de
Inventor
Revathi R. Tomko
Louisa D. Dicola
Lorette Madigan
David J. Tetzlaf
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Sherwin Williams Co
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Sherwin Williams Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2270/00—Compositions for creating interpenetrating networks

Definitions

  • EP 0 663 412 A1 discloses aqueous self cross-linkable resin composition
  • aqueous self cross-linkable resin composition comprising an aqueous dispersion of a polyurethane polymer having anionic salt groups as chain pendent functional groups and a vinyl polymer having chain pendent acetoacetoxyalkylester groups.
  • the polyurethane polymer and the vinyl polymer are self cross-linkable.
  • European Patent Application 94309136.3 discloses the use of a polymeric blend of a latex, an acid-functional alkali-soluble resin and an aminosilane in order to provide adhesion of coatings over chalky substrates.
  • the polymer network, and coatings containing the polymer network, produced by the present invention have particular utility over chalky substrates including previously painted wood, concrete, cement, brick, vinyl and aluminum siding and the like. They can also be applied over metal, concrete, wood, plastic, leather, vinyl and other unchalked substrates.
  • composition of the present invention may contain two or more waterborne component, such as, for example, a vinyl latex and a silicone emulsion.
  • the active-hydrogen containing composition is preferably a diol selected from the group consisting of polyester diols, polyether diols, polyacetal diols, polyamide diols, polyester polyamide diols, poly(alkylene ether) diols, polythioether diols and polycarbonate diols.
  • Suitable polyester diols, polyester amide diols and polyamide diols are preferably saturated and are obtained, for example, from the reaction of saturated or unsaturated polycarboxylic acids with saturated or unsaturated polyhydric alcohols.
  • Suitable carboxylic acids for preparing these compounds include, for example, adipic acid, succinic acid, phthalic acid, terephthalic acid, and maleic acid.
  • Suitable polyhydric alcohols for preparing the polyester diols include, for example, ethylene glycol. 1.2-propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, and trimethylolpropane.
  • a suitable amino alcohol for preparing polyester amide diols is, for example, ethanolamine.
  • Suitable diamines for preparing polyesteramide diols and polyamide diols are, for example, ethylene diamine and hexamethylene diamine.
  • the most preferred difunctional active-hydrogen containing starting materials are a combination of 1) the polyester diols formed from the reaction of saturated and unsaturated dihydric alcohols such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,4-butenediol, 1,6-hexanediol, furan dimethanol, and cyclohexane dimethanol with saturated and unsaturated polycarboxylic acids such as maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, adipic acid, isophthalic acid, terephthalic acid, phthalic anhydride, dimethyl terephthalate, dimer acids and the like; and 2) a diol containing hydrophilic groups.
  • saturated and unsaturated dihydric alcohols such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,4-but
  • the ionizable groups of the polyurethane prepolymer are converted by combining the prepolymer with water containing a tertiary amine.
  • Tertiary amines that may be used include triethylamine, trimethylamine, triisopropyl amine, tributyl amine, triethylene diamine, N,N-dimethyl-cyclohexyl amine, N,N-dimethylstearyl amine, N,N-dimethyl aniline, N-methylmorpholine, N-ethylmorpholine, N-methylpiperazine, N-methylpyrrolidine, N,N-dimethyl-ethanol amine, N,N-diethyl-etanol amine, triethanol amine, N-methyldiethanol amine, dimethylaminopropanol, 2-methoxyethyldimethyl amine, N-hydroxyethylpiperazine, 5-diethylamino-2-pentanone and mixtures thereof
  • the weight ratio of polyurethane prepolymer component to waterborne polymer component is generally in the range of 1:99 to 99:1, preferably from 1:4 to 1:1.
  • a reaction vessel equipped with a nitrogen blanket was charged with 30.0g of n-methyl pyrrolidone, 180.0g of Rucoflex TM 1015-120 polyester diol mixture. 25.0g of dimethylolpropionic acid, 6.0g of trimethylolpropane, 10.0g of 1.4-cyclohexane dimethanol and approximately 1.0g of dibutyl tin dilaurate (10% solution in n-methyl pyrrolidone). The contents of the vessel were stirred and the temperature was increased to about 90°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Graft Or Block Polymers (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Liquid Developers In Electrophotography (AREA)

Claims (18)

  1. Ein Verfahren zur Erzeugung einer Beschichtungszusammensetzung, wobei das Verfahren umfasst:
    a) Herstellen eines funktionalisierten Polyurethan-Vorpolymers, welches anhängende ionisierbare Gruppen enthält, die anschließend ionisiert werden, wobei das Vorpolymer wenigstens eine funktionelle Gruppe enthält, ausgewählt aus Hydroxy, Isocyanat, Acetoacetoxy und n-Methylol,
    b) Dispergieren des funktionalisierten Polyurethan-Vorpolymers in Wasser, um eine Polyurethan-Vorpolymerdispersion zu bilden,
    c) Zugeben einer wässrigen Polymerkomponente zu der Polyurethan-Vorpolymerdispersion, wobei die wässrige Polymerkomponente keine funktionellen Gruppen enthält, die mit Amin-, Isocyanat-, Hydroxyl- oder Carboxylgruppen reaktiv sind, und
    d) Kettenverlängern des funktionalisierten Polyurethan-Vorpolymers mit einem Kettenverlängerer in Gegenwart der wässrigen Polymerkomponente, wobei das wässrige Polymer ausgewählt ist aus der Gruppe, bestehend aus Vinylkautschukemulsionen, Acrylpolymeren, Alkydacryldispersionen, wasserreduzierbaren Alkyden, Alkydemulsionen, Polyurethandispersionen, Polyurethanacryldispersionen, Fluorpolymeremulsionen, Polyesteremulsionen, Silikonemulsionen, Polyethylenemulsionen, Polyamiddispersionen und Mischungen davon.
  2. Das Verfahren nach Anspruch 1, wobei das funktionalisierte Polyurethan-Vorpolymer das Reaktionsprodukt einer aktiven Wasserstoff enthaltenden Zusammensetzung und einer isocyanatfunktionellen Zusammensetzung umfasst.
  3. Das Verfahren nach Anspruch 2, wobei die aktiven Wasserstoff enthaltende Zusammensetzung ausgewählt ist aus der Gruppe, bestehend aus Diolen, Triolen, Aminen, Aminoalkoholen, Mercaptanen und Mischungen davon.
  4. Das Verfahren nach Anspruch 2, wobei die isocyanatfunktionelle Zusammensetzung ein Diisocyanat umfasst.
  5. Das Verfahren nach Anspruch 4, wobei das Diisocyanat ausgewählt ist aus der Gruppe, bestehend aus aromatischen, cycloaliphatischen und aliphatischen Diisocyanaten und Mischungen davon.
  6. Das Verfahren nach Anspruch 5, wobei das Diisocyanat ausgewählt ist aus der Gruppe, bestehend aus 1,6-Hexamethylendiisocyanat, 2,4-Toluoldiisocyanat, 2,6-Toluoldiisocyanat, 1,4-Phenylendiisocyanat, 4,4'-Diphenylmethandiisocyanat, 2,4-Diphenylmethandiisocyanat, Isophorondiisocyanat, Cyclohexan-1,4-diisocyanat, 4,4'-Dicyclohexylmethandiisocyanat, p-Xylylendiisocyanat, meta-1,1,3,3-Tetramethylxylylendiisocyanat und Mischungen davon.
  7. Das Verfahren nach Anspruch 1, wobei die wässrige Polymerkomponente wenigstens ein wässriges Polymer umfasst.
  8. Das Verfahren nach Anspruch 1, wobei das Polyurethan-Vorpolymer funktionelle Gruppen enthält, welche bei der Filmbildung und der Einwirkung von Umgebungsbedingungen vernetzen.
  9. Das Verfahren nach Anspruch 8, wobei die funktionellen Gruppen ausgewählt sind aus der Gruppe, bestehend aus Fettaminen, Allylaminen, Diallylaminen, ethoxylierten Allylaminen, ethoxylierten Allylalkoholen, Fettalkohlen, Allylalkoholen, Trimethylolpropanmono- und -diallylether, Hydroxyethylacrylat, Hydroxyethylmethacrylat, durch Alkoholyse von Trockenölen mit Polyolen oder durch Reaktion von Trockenfettsäuren mit Polyolen erhaltenen Mono- und Diglyceriden, acetoacetathaltigen Materialien, anhydridfunktionellen Trockenölen, Trialkoxysilan und epoxyfunktionellen Ölen.
  10. Das Verfahren nach Anspruch 1, wobei die wässrige Polymerkomponente einen Vinylkautschuk umfasst.
  11. Das Verfahren nach Anspruch 2, wobei das Verhältnis der Moläquivalente NCO zu den Gesamtäquivalenten an aktivem Wasserstoff zwischen 1,01:1 bis 2,0:1 beträgt.
  12. Das Verfahren nach Anspruch 2, wobei zwischen 1 Gew.-% und 10 Gew.-% des Gewichts an Polyurethan-Vorpolymer-Feststoffen aus aktiven Wasserstoff enthaltenden Zusammensetzungen mit wenigstens einer anhängenden ionisierbaren Gruppe besteht, wobei die aktiven Wasserstoff enthaltende Zusammensetzung ausgewählt ist aus der Gruppe, bestehend aus Diolen, Aminen und Mercaptanen, und wobei die anhängende ionisierbare Gruppe ausgewählt ist aus der Gruppe, bestehend aus Carbonsäure, Sulfonsäure, Phosphorsäure, Ammoniumsalze, Phosphoniumsalze und Sulfoniumsalze.
  13. Das Verfahren nach Anspruch 2, wobei die aktiven Wasserstoff enthaltende Zusammensetzung ein Diol ist, ausgewählt aus der Gruppe, bestehend aus Polyesterdiolen, Polyetherdiolen, Polyacetaldiolen, Polyamiddiolen, Polyesterpolyamiddiolen, Poly(alkylenether)diolen, Polythioetherdiolen, Polycarbonatdiolen, Bisphenol A und Mischungen davon.
  14. Das Verfahren nach Anspruch 1, wobei der Kettenverlängerer ausgewählt ist aus der Gruppe, bestehend aus Polyolen, Aminoalkoholen, primären oder sekundären aliphatischen, alicyclischen, aromatischen und heterocyclischen Aminen, aminfunktionellen Silanen, aminfunktionellen Silikonen, wasserdispergierbaren oder emulgierbaren Polyisocyanaten und Polyaldehyden.
  15. Ein Verfahren zur Herstellung einer Oberflächenbeschichtung mit Kreidehaftung auf verwitterten Oberflächen, wobei das Verfahren umfasst:
    a) Herstellung eines isocyanatfunktionellen Polyurethan-Vorpolymers, welches anhängende ionisierbare Gruppen enthält, die anschließend ionisiert werden,
    b) Dispergieren des isocyanatfunktionellen Polyurethan-Vorpolymers in Wasser, um eine Polyurethan-Vorpolymerdispersion zu bilden,
    c) Zugeben einer wässrigen Polymerkomponente zu der isocyanatfunktionellen Polyurethan-Vorpolymerdispersion, wobei die wässrige Polymerkomponente keine funktionellen Gruppen enthält, die mit Amin-, Isocyanat-, Hydroxyl- oder Carboxylgruppen reaktiv sind, und
    d) Kettenverlängern des isocyanatfunktionellen Polyurethan-Vorpolymers mit einem Kettenverlängerer in Gegenwart der wässrigen Polymerkomponente, wobei das wässrige Polymer ausgewählt ist aus der Gruppe, bestehend aus Vinylkautschukemulsionen, Acrylpolymeren, Alkydacryldispersionen, wasserreduzierbaren Alkyden, Alkydemulsionen, Polyurethandispersionen, Polyurethanacryldispersionen, Fluorpolymeremulsionen, Polyesteremulsionen, Silikonemulsionen, Polyethylenemulsionen, Polyamiddispersionen und Mischungen davon.
  16. Das Verfahren nach Anspruch 15, wobei das Polyurethan-Vorpolymer funktionelle Gruppen enthält, welche bei der Filmbildung und der Einwirkung von Umgebungsbedingungen vernetzen.
  17. Das Verfahren nach Anspruch 16, wobei die funktionellen Gruppen ausgewählt sind aus der Gruppe, bestehend aus Fettaminen, Allylaminen, Diallylaminen, ethoxylierten Allylaminen, ethoxylierten Allylalkoholen, Fettalkohlen, Allylalkoholen, Trimethylolpropanmono- und -diallylether, Hydroxyethylacrylat, Hydroxyethylmethacrylat, durch Alkoholyse von Trockenölen mit Polyolen oder durch Reaktion von Trockenfettsäuren mit Polyolen erhaltenen Mono- und Diglyceriden, acetoacetathaltigen Materialien, anhydridfunktionellen Trockenölen, Trialkoxysilan und epoxyfunktionellen Ölen.
  18. Das Verfahren nach Anspruch 15, wobei der Kettenverlängerer ausgewählt ist aus der Gruppe, bestehend aus Polyolen, Aminoalkoholen, primären oder sekundären aliphatischen, alicyclischen, aromatischen und heterocyclischen Aminen, aminfunktionellen Silanen und aminfunktionellen Silikonen.
EP99928811A 1998-06-23 1999-06-22 Teil-interpenetrierende polymernetzwerke Expired - Lifetime EP1088014B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US102867 1998-06-23
US09/102,867 US6022925A (en) 1998-06-23 1998-06-23 Partial interpenetrating networks of polymers
PCT/US1999/013938 WO1999067311A1 (en) 1998-06-23 1999-06-22 Partial interpenetrating networks of polymers

Publications (2)

Publication Number Publication Date
EP1088014A1 EP1088014A1 (de) 2001-04-04
EP1088014B1 true EP1088014B1 (de) 2009-04-22

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US (1) US6022925A (de)
EP (1) EP1088014B1 (de)
JP (1) JP2002518564A (de)
CN (1) CN1144826C (de)
AT (1) ATE429457T1 (de)
AU (1) AU752139B2 (de)
BR (1) BR9911446B1 (de)
CA (1) CA2335579C (de)
DE (1) DE69940773D1 (de)
ID (1) ID27310A (de)
WO (1) WO1999067311A1 (de)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2772778B1 (fr) * 1997-12-19 2002-03-29 Ato Findley Sa Adhesif polyurethane reticulable par l'humidite, procede de collage d'un textile et d'un materiau cellulaire au moyen dudit adhesif et assemblage colle ainsi obtenu
WO2000052083A1 (en) * 1999-03-03 2000-09-08 Eastman Chemical Company Silicone polymer diol compositions and condensation polymer/silicone polymer blends
US7429220B2 (en) * 2001-04-13 2008-09-30 Acushnet Company Golf balls containing interpenetrating polymer networks
US7297750B2 (en) * 2001-05-02 2007-11-20 Bridgestone Corporation Clear paint for golf balls and golf ball
CA2447132C (en) * 2001-05-14 2008-10-07 Omnova Solutions Inc. Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups
CA2453818C (en) 2001-07-25 2008-05-06 The Sherwin-Williams Company Water-based water repellent coating compositions
US7829631B2 (en) * 2002-09-18 2010-11-09 Valspar Sourcing, Inc. Self-crosslinkable waterborne coating composition
US20070027249A1 (en) * 2003-08-13 2007-02-01 Valspar Sourcing, Inc. Water-based polyurethane-polyethylene compositions
US20050148683A1 (en) * 2003-12-29 2005-07-07 Reid-Gree John D. Building material having an aggregate processed to remove contaminants therein
US20050197480A1 (en) * 2004-03-05 2005-09-08 Temple Rodger G. Barrier coating comprising a polyurethane dispersion and elastomeric material
US20090088846A1 (en) 2007-04-17 2009-04-02 David Myung Hydrogel arthroplasty device
DE102005019430A1 (de) * 2005-04-25 2006-10-26 Bayer Materialscience Ag N-Methylpyrrolidon-freie Polyurethan-Dispersionen auf Basis von Dimethylolpropionsäure
US7642314B2 (en) * 2005-12-30 2010-01-05 Columbia Insurance Company Emulsion polymers having multimodal molecular weight distributions
DE102006022842A1 (de) * 2006-05-16 2007-11-22 Wacker Chemie Ag Über Methylolgruppen vernetzbare Siliconpolymere
WO2008016843A1 (en) 2006-07-31 2008-02-07 Lubrizol Advanced Materials, Inc. Aqueous dispersions of polyurethane compositions with ketone-hydrazide
US9234068B2 (en) * 2007-10-02 2016-01-12 The Hong Kong University of Science and Technologhy Method for preparing aqueous polyacrylate modified polyurethane dispersions
WO2009100341A1 (en) 2008-02-08 2009-08-13 3M Innovative Properties Company Semi-ipn polyurethane/polyurea protective films
WO2010005992A1 (en) * 2008-07-07 2010-01-14 Biomimedica, Inc. Hydrophilic interpenetrating polymer networks derived from hydrophobic polymers
US20120209396A1 (en) 2008-07-07 2012-08-16 David Myung Orthopedic implants having gradient polymer alloys
US9752022B2 (en) 2008-07-10 2017-09-05 Avery Dennison Corporation Composition, film and related methods
EP2323670A4 (de) 2008-08-05 2013-12-25 Biomimedica Inc Polyurethan-gepfropfte hydrogele
MX338179B (es) * 2008-12-22 2016-04-06 Sherwin Williams Co Redes polimericas interpenetrantes fotocurables.
EP2542409B1 (de) 2010-03-04 2018-12-19 Avery Dennison Corporation Pvc-freie folie und pvc-freies folienlaminat
US20130217829A1 (en) 2010-08-27 2013-08-22 David Myung "hydrophobic and hydrophilic interpenetrating polymer networks derived from hydrophobic polymers and methods of preparing the same"
TW201224056A (en) 2010-10-29 2012-06-16 Lubrizol Advanced Mat Inc Aqueous cationic polyurethane dispersions
WO2013052105A2 (en) 2011-10-03 2013-04-11 Biomimedica, Inc. Polymeric adhesive for anchoring compliant materials to another surface
AU2012340699A1 (en) 2011-11-21 2014-06-19 Biomimedica, Inc. Systems, devices, and methods for anchoring orthopaedic implants to bone
US9856435B2 (en) 2012-09-04 2018-01-02 Lubrizol Advanced Materials, Inc. Polyurethane/polyacrylic hybrid dispersions for shine applications in home care
US9045582B2 (en) * 2013-10-29 2015-06-02 Uop Llc Cross-linked rubbery polyurethane-ether membranes for separations
BR112016014704A8 (pt) 2013-12-30 2020-05-26 Avery Dennison Corp película protetora, laminado de película, gráfico de publicidade ou informativo, método de produção de uma película protetora, uso de uma película protetora ransparente e rolo ou folha de gráfico de publicidade
WO2016016139A1 (de) * 2014-08-01 2016-02-04 Basf Se Verfahren zur herstellung und verwendung wässriger polyurethandispersionen sowie deren verwendung in beschichtungsmitteln
US11077228B2 (en) 2015-08-10 2021-08-03 Hyalex Orthopaedics, Inc. Interpenetrating polymer networks
JP6610935B2 (ja) * 2015-10-07 2019-11-27 Ｄｉｃ株式会社 建材用コーティング剤
CN109642003B (zh) * 2016-05-10 2022-02-15 澳大利亚国立大学 互穿聚合物网络
CN107434381B (zh) * 2016-05-27 2021-01-05 立邦涂料（中国）有限公司 一种特种地坪涂料水性聚氨酯砂浆复合涂料及其制法和应用
WO2018235921A1 (ja) * 2017-06-22 2018-12-27 トーヨーポリマー株式会社 ポリウレタン水分散体、ポリウレタン水分散体の製造方法、水系塗料組成物および塗膜
CN108017972B (zh) * 2017-11-24 2020-04-07 鹤山市信兴化工有限公司 有机硅改性丙烯酸聚氨酯杂合乳液及由其制成的水性涂料
WO2019162206A2 (de) * 2018-02-21 2019-08-29 Basf Se Verfahren zur herstellung von mit klebstoff beschichteten artikeln
US10869950B2 (en) 2018-07-17 2020-12-22 Hyalex Orthopaedics, Inc. Ionic polymer compositions
CN110305287A (zh) * 2019-07-22 2019-10-08 安徽聚合辐化化工有限公司 一种光亮水性聚氨酯及其制备方法
US11801143B2 (en) 2021-07-01 2023-10-31 Hyalex Orthopaedics, Inc. Multi-layered biomimetic osteochondral implants and methods of using thereof
CN114231109A (zh) * 2021-12-20 2022-03-25 蓝帆新材料技术(广州)有限公司 一种具有互穿网络结构的镀锌钢板用水性耐指纹涂料
EP4480977A1 (de) * 2023-06-23 2024-12-25 CertainTeed LLC Beschichtungen auf polyurethanbasis und beschichtete substrate
CN119019893B (zh) * 2024-10-30 2025-03-14 四川锦睿管业有限公司 聚乙烯基复合涂料及其制备方法、应用

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE757936A (fr) * 1969-10-23 1971-04-01 Bayer Ag Procede de preparation de polymeres anioniques modifies en emulsion
US4318833A (en) * 1980-05-16 1982-03-09 Inmont Corporation Water reducible coating compositions of acrylic-urethane polymers
IT1153000B (it) * 1982-07-01 1987-01-14 Resem Spa Dispersioni acquose di poliuretani da oligouretani aventi gruppi terminali insaturi
NL8401785A (nl) * 1984-06-04 1986-01-02 Polyvinyl Chemie Holland Werkwijze voor de bereiding van een waterige dispersie van urethan-acrylaat entcopolymeren, alsmede aldus verkregen stabiele waterige dispersie.
US4644030A (en) * 1985-02-01 1987-02-17 Witco Corporation Aqueous polyurethane - polyolefin compositions
US4722965A (en) * 1986-02-24 1988-02-02 Reichhold Chemicals, Inc. Chalk adhesion polymer composition and method of preparation
GB8721537D0 (en) * 1987-09-14 1987-10-21 Polyvinyl Chemical Ind Aqueous dispersions
US5314942A (en) * 1987-09-14 1994-05-24 Ici Americas, Inc. Aqueous dispersions
GB8721536D0 (en) * 1987-09-14 1987-10-21 Polyvinyl Chemical Ind Aqueous dispersions
GB8721538D0 (en) * 1987-09-14 1987-10-21 Polyvinyl Chemie Holland Bv Aqueous dispersions
EP0353797A1 (de) * 1988-06-30 1990-02-07 Akzo N.V. Funktionalisiertes Polyurethan, verwendbar zur Herstellung von wässrigen Polymerhybriddispersionen
IT1227389B (it) * 1988-07-07 1991-04-08 Mini Ricerca Scient Tecnolog Dispersioni acquose di polimeri uretano-acrilici e loro impiego come vernici.
US5371133A (en) * 1990-09-12 1994-12-06 National Starch And Chemical Investment Holding Corporation Process for preparing urethane/acrylic-or-vinyl latexes
US5202378A (en) * 1991-03-08 1993-04-13 The Glidden Company Process for producing an exterior latex paint having improved chalk adhesion
US5173526A (en) * 1991-04-26 1992-12-22 Air Products And Chemicals, Inc. Aqueous polyurethane-vinyl polymer dispersions for coating applications
KR950018342A (ko) * 1993-12-15 1995-07-22 윌리엄 이. 램버트 3세 백악질 기질에 대한 코팅제의 접착력을 개선시키는 혼합조성물
GB9400663D0 (en) * 1994-01-14 1994-03-09 Ucb Sa Aqueous polyurethane resin compositions
US5763529A (en) * 1994-03-31 1998-06-09 Cytec Technology Corp. Interpenetrating polymer network compositions

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JP2002518564A (ja) 2002-06-25
CN1144826C (zh) 2004-04-07
BR9911446B1 (pt) 2009-01-13
EP1088014A1 (de) 2001-04-04
DE69940773D1 (de) 2009-06-04
ID27310A (id) 2001-03-22
ATE429457T1 (de) 2009-05-15
CN1306548A (zh) 2001-08-01
WO1999067311A1 (en) 1999-12-29
AU4579599A (en) 2000-01-10
CA2335579C (en) 2005-09-27
AU752139B2 (en) 2002-09-05
CA2335579A1 (en) 1999-12-29
US6022925A (en) 2000-02-08
BR9911446A (pt) 2001-03-20

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